Hydrochloric Acid → Gon-4-en-3-one, 13-ethyl-17-hydroxy-, (17beta)-(+-)-

HRID 1415000Notes

Reaction equation

HRID 1415000 reaction equation
[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C:12]4[CH2:13][CH2:14][C:15](=[O:20])[CH2:16][C:17]=4[CH2:18][CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C@@H:4]2[OH:21])[CH3:2].CO.Cl>O>[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C@@H:12]4[C:17]([CH2:18][CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C@@H:4]2[OH:21])=[CH:16][C:15](=[O:20])[CH2:14][CH2:13]4)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 1111976613beta-Ethyl-17beta-hydroxy-gon-5(10)-en-3-one

Product 1

HCID 10039774Gon-4-en-3-one, 13-ethyl-17-hydroxy-, (17beta)-(+-)-Yield 66.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Stir 13β-ethyl-17β-hydroxy-gon-5(10)-en-3-one (300 mg.) for 2 hours under nitrogen at room temperature with methanol (10 cc.)-11N hydrochloric acid (0.5 cc.)-water (0.3 cc.). Add sodium bicarbonate (2 g.) and ether (50cc.), filter the mixture, evaporate the ether and recrystallize the residue from ethyl acetate-ether to give 13β-ethyl-17β-hydroxy-gon-4-en-3-one (0.2 g.), m.p. 147°-149°; ultraviolet absorption peak at 242 mμ (ε 17,600); infrared absorption peaks at 2.78, 2.90, 6.02, 6.17.

Workup

  1. filtrationAdd sodium bicarbonate (2 g.) and ether (50cc.), filter the mixture
  2. customevaporate the ether
  3. customrecrystallize the residue from ethyl acetate-ether

Sources & evidence

ORD record
ord-3fc281c230c949d18eb85639ddcdac97
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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